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Reductive Dicarbofunctionalization of Unactivated Internal Alkenes via Iron Catalysis
Haoran Hou1, Siyu Wang1, Hong Huang2
1Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P. R. China.
None:
We report an iron-catalyzed reductive fluoroalkylalkenylation of unactivated internal alkenes. Various fluoroalkyl bromides and the Togni reagent undergo this three-component coupling reaction smoothly, generating a diverse array of homoallylic fluoroalkanes with high efficiency. The method is notable for its ability to proceed without the need for directing or activating groups, offering excellent functional group tolerance, a broad substrate scope, and good applications in the late-stage difunctionalization of biorelevant molecules. Preliminary mechanistic studies suggest that fluoroalkyl radicals are involved in the catalytic cycle, which operates via a radical cascade addition pathway.
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